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Studies towards total synthesis of MPC1001F - a triketopiperazine- dihydrooxepin natural product

  • Author / Creator
    Bhattacharyya, Dipanjan
  • The thesis describes synthetic studies towards MPC1001F, a triketopiperazine-dihydrooxepin natural product. Another related member of this class of natural products is MPC1001 with an epidithiodioxopiperazine core and potent antitumor activity. Our goal was to construct the molecular skeleton of the comparatively simpler MPC1001F first so that the knowledge gained during this project can be applied to the synthesis of the more complex MPC1001. None of these MPC natural products have yet been synthesized. An enantioselective synthesis of the tricyclic core of MPC1001F is discussed first, by a route which followed the strategy on a related core, already established in our group. The main synthetic challenges encountered in this route are discussed. These involved oxidation of an alcohol without epimerization next to the resulting aldehyde, oxidation of an alcohol in the presence of selenium, and construction of a tetrahydrooxepin ring via a conjugate addition-elimination process. An insurmountable obstacle in this route led us to explore a different strategy. In the next section, several unsuccessful approaches towards the core, starting from already-synthesized intermediates from the first route, are described. Finally, I designed a new short enantioselective sequence towards the core structure which is shown in the third section of this thesis. The synthesis of the tricyclic core has been achieved following this new strategy. The last few steps to the fully functionalized core are still being studied.

  • Subjects / Keywords
  • Graduation date
    2013-06
  • Type of Item
    Thesis
  • Degree
    Doctor of Philosophy
  • DOI
    https://doi.org/10.7939/R3J67972C
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Doctoral
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Clive, D. L. J. (Chemistry)
  • Examining committee members and their departments
    • Li, Liang (Chemistry)
    • Lowary, Todd L. (Chemistry)
    • Narain, Ravin (Chemical and Materials Engineering)
    • Dmitrienko G. (University of Waterloo, Chemistry, External Examiner)
    • West, Frederick G. (Chemistry)